Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/12—Preparations containing hair conditioners
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/416—Quaternary ammonium compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
  • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
  • C07D295/182—Radicals derived from carboxylic acids
  • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S424/00—Drug, bio-affecting and body treating compositions
  • Y10S424/02—Resin hair settings
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S424/00—Drug, bio-affecting and body treating compositions
  • Y10S424/04—Dandruff

Definitions

• the present invention relates to compositions which contain quaternary ammonium derivatives and which are intended for the treatment of keratin substances, such as the hair and skin.
• compositions in particular cosmetic compositions, which are intended to be used for the treatment of the hair and which are based on quaternary ammonium derivatives are already known.
• These compositions which are used in particular as post-shampoo rinsing products, are generally presented in the form of a milky liquid, a balm or a cream; they have the disadvantage of weighing down the treated hair, this resulting from both the nature of the quaternary ammonium derivatives used and from the adjuvants required to impart the desired appearance and viscosity, and also the desired softness effects, to these derivatives.
• compositions are preferably used only in the treatment of dry or damaged hair.
• Bis-(quaternary ammonium) derivatives have principally been proposed for use in the dyeing of polyacrylonitrile fibres or in the treatment of synthetic or cellulosic textile materials.
• compositions containing bis-(quaternary ammonium) derivatives with two lipophilic chains for the treatment of natural keratin substances, especially human hair, imparts more lightness to the hair than the use of the quaternary ammonium derivatives previously proposed for this purpose; these compositions can thus be applied to any type of hair (dry, normal or naturally greasy hair).
• the compounds used in the present invention can be used in very small amounts for improving the combing-out, the softness and the glossiness of the hair, and they also possess a good tolerance.
• the invention thus relates to compositions which are intended to be used for the treatment of natural keratin substances and which contain at least one bis-(quaternary ammonium) derivative with two lipophilic chains as well as to processes for the treatment of natural keratin substances with the abovementioned compositions.
• R denotes a linear or branched alkyl or alkenyl group having 12 to 18 carbon atoms, or a mixture of such groups, and those in which R represents a mixture of aliphatic groups derived from fatty chains of natural products, such as tallow, copra and lanoline.
• A forms a heterocyclic group together with the adjacent nitrogen atoms, it preferably denotes a piperazinyl group.
• the invention also provides, as new compounds, the compounds of formula (I) with the proviso that n is greater than 3 if R denotes an alkyl group having 10 to 18 carbon atoms.
• the compounds which are more particularly preferred according to the invention result from the condensation of bis-chloroacetyl-1, 3-diaminopropane, bis-chloroacetylpiperazine, bis-chloroacetylethylenediamine or bis-chloroacetylhexamethylenediamine with N,N-dimethyl-tallow alkyl-amine or with N,N-dimethylalkyl (C 12 -C 14 )-amine.
• the compounds corresponding to the formula (I) possess valuable properties when used in the treatment of natural keratin substances and in particular hair.
• the invention thus relates to the use of the compounds of the formula (I) for the treatment of keratin substances, such as hair, skin, fingernails and body hair.
• compositions which are intended for use in the treatment of the abovementioned keratin substances are preferably aqueous compositions which can be used as such; however, they can also contain adjuvants which are normally used in compositions for the treatment of keratin substances.
• these cosmetic compositions are typically presented in the form of an aqueous, alcoholic or aqueous-alcoholic solution or in the form of a cream, a gel, an emulsion or a powder, or they can be packaged in an aerosol in the presence of a propellant.
• the adjuvants present in these compositions are cosmetically acceptable adjuvants, such as non-ionic, anionic, cationic or amphoteric surface-active agents which are well known in the art, animal, mineral, vegetable or synthetic oils or waxes, fatty alcohols, anionic, cationic, non-ionic or amphoteric resins which are normally used in cosmetics, emulsifiers, sun filters, organic solvents, thickeners, opacifying agents, preservatives, sequestering agents, antioxidants, perfumes, agents for imparting pearlescence, dyestuffs, pH modifiers, reducing agents, electrolytes, oxidizing agents, natural substances, protein derivatives, anti-seborrhea agents, anti-dandruff agents, restructuring agents, and active substances which can have an action in the treatment, care or protection of the skin or hair.
• cosmetically acceptable adjuvants such as non-ionic, anionic, cationic or amphoteric surface-active agents which are well known in the art, animal,
• compositions can be used, in particular, as shampoos, as coloring products, as rinsing lotions to be applied before or after shampooing, before or after coloring or bleaching, or before or after perming, as styling or restructuring lotions, as treating lotions, such as anti-seborrhea or anti-dandruff lotions, as brushing lotions, as hair lacquers, as wavesetting lotions and as perming compositions.
• the compounds When the compounds are applied in the treatment of the hair, either in pre-treating or post-treating lotions, or during the actual treatment, such as shampooing, dyeing, bleaching, wavesetting or perming, they substantially improve the properties of the hair by facilitating the combing-out of the hair when wet or dry, and by imparting glossiness, softness, suppleness, manageability and antistatic properties to the hair when dry.
• the hair treated in this way is light, springy and bulky, these being desirable properties for normal or naturally greasy hair.
• the bis-(quaternary ammonium) derivatives with two lipophilic chains, of the formula I should, of course, be used in the compositions according to the invention in sufficient amounts to obtain the desired result, generally in an amount from 0.01 to 10% by weight, preferably 0.1 to 4% by weight.
• these compounds are very valuable when used as pre-treating agents before an anionic and/or non-ionic shampoo or before an oxidation dyestuff, the latter itself being followed by an anionic and/or non-ionic shampoo.
• the bis-(quaternary ammonium) derivatives with two lipophilic chains, of the formula (I), also give very advantageous results when used as post-treating agents and in particular as post-shampoo rinsing lotions and as wavesetting or shaping lotions, restructuring lotions, brushing lotions, styling gels and treating lotions.
• compositions for the hair include in particular:
• compositions for the treatment or the pre-treatment or post-treatment of the hair are optionally followed by rinsing, after an interval of, say, 1 to 30 minutes.
• the compounds of the formula (I) are preferably present in a proportion of 0.01 to 10% by weight, preferably 0.1 to 4% by weight, expressed in terms of active ingredient, relative to the total weight of the composition.
• the pH is generally from 2 to 10.
• the treating compositions or pre-treating or post-treating compositions can contain various adjuvants, in particular polyethylene glycols and their derivatives, anionic, cationic, amphoteric or non-ionic resins which are normally used in cosmetic compositions for the hair, pH modifiers, protein derivatives, such as quaternized or non-quaternised protein hydrolysates, natural substances, such as plant extracts, fatty alcohols, such as optionally polyoxyethyleneated or polyglycerolated cetyl, stearyl, cetyl/stearyl or oleyl alcohol, animal, vegetable, mineral or synthetic oils or waxes, such as optionally oxyethyleneated petrolatum, maize oil, wheatgerm oil, olive oil, soya bean oil, castor oil or avocado
• Shampoos which are essentially characterized in that they contain at least one anionic, non-ionic or amphoteric surface-active agent or a mixture thereof, and a compound of the formula (I), in an aqueous medium.
• These compositions can also contain various adjuvants which are normally used in this type of composition, such as cationic surface-active agents, dyestuffs in the case of coloring shampoos, preservatives, thickeners, foam stabilizers, synergistic agents, softening agents, sequestering agents, one or more cosmetic resins, perfumes, protein derivatives, natural substances and oils.
• the concentration of detergent is generally 2 to 50% by weight.
• non-ionic detergents there may be mentioned, in particular, the products resulting from the condensation of a monoalcohol, an alpha-diol, an alkylphenol, an amide or a diglycolamide with glycidol, such as the non-ionic surface-active agents described in French Pat. Nos.
• polyoxyethyleneated or polyglycerolated alcohols alkylphenols or fatty acids with linear fatty chains having 8 to 18 carbon atoms and most frequently containing 2 to 30 mols of ethylene oxide, copolymers of ethylene oxide and propylene oxide, products resulting from the condensation of ethylene oxide and propylene oxide with fatty alcohols, polyoxyethyleneated fatty amides, polyoxyethyleneated fatty amines, ethanolamides, fatty acid esters of glycol, fatty acid esters of sorbitol and fatty acid esters of sucrose.
• anionic surface-active agents which can optionally be used with the non-ionic surface-active agents, are chosen, in particular, from amongst the alkali metal salts, the ammonium salts, the amine salts or the aminoalcohol salts of the following compounds: alkyl-sulphates, alkyl-ether-sulphates, alkylamide-sulphates and alkylamido-ether-sulphates, alkylaryl-polyethersulphates and monoglyceride-sulphates; alkyl-sulphonates, alkylamidesulphonates, alkylarylsulphonates and ⁇ -olefinesulphonates; alkylsulphosuccinates, alkyl-ethersulphosuccinates and alkylamide-sulphosuccinates; alkylsulphosuccinamates; alkyl-sulphoacetates and alkylpolyglycerol-carboxylates; alkyl-phosphates and alkyl-phosphat
• substituent Alk corresponds to a linear chain having from 12 to 18 carbon atoms and in which n is an integer from 5 to 15. It is of course also possible to use other anionic detergents well known in the art.
• amphoteric surface-active agents which can be used, there may be mentioned, more particularly, alkylamino-monopropionates and -dipropionates of betaines such as N-alkylbetaines, N-alkylsulphobetaines and N-alkylamidobetaines, cycloimidinium compounds, such as alkylimidazolines, and asparagine derivatives.
• the alkyl group in these surface-active agents preferably possesses 1 to 22 carbon atoms.
• Hair-dyeing compositions such as dyeing compositions which function by an oxidation method and contain oxidation dyestuff precursors, such as those of the para- or ortho-type, and optionally couplers, in a medium which is basic and preferably has a pH of 8 to 11, and which can also contain direct dyestuffs which are well known in the art, or dyeing compositions which are intended for direct or semi-permanent coloration and contain direct dyestuffs, such as nitrobenzene derivatives, azo dyestuffs, anthraquinone dyestuffs, indamines, indoanilines or indophenols.
• direct dyestuffs such as nitrobenzene derivatives, azo dyestuffs, anthraquinone dyestuffs, indamines, indoanilines or indophenols.
• Bleaching compositions which consist of carriers in the form of powders, solutions, emulsions or gellable liquids, or in the form of creams, containing at least one bleaching agent, such as hydrogen peroxide or other peroxides or solutions of per-salts(e.g. persulphates, perborates or percarbonates), and at least one compound of the formula (I).
• at least one bleaching agent such as hydrogen peroxide or other peroxides or solutions of per-salts(e.g. persulphates, perborates or percarbonates), and at least one compound of the formula (I).
• the bleaching compositions are in the form of creams or gellable liquids, which are similar to those described above in the context of the dyeing compositions. These are intended to be diluted at the time of use with a solution of hydrogen peroxide and/or of per-salts and/or of other peroxides.
• the carriers generally contain an alkalizing agent, such as ammonia.
• bleaching compositions can be applied using conventional techniques.
• the conventional technique for perming the hair consists, in a first stage, in opening the S--S bonds in the keratin of the hair, using a composition containing a reducing agent, and then, in a second stage, preferably after having rinsed the head of hair, in re-forming the said S--S bonds by applying an oxidizing composition to the hair which has been subjected to reduction, so as to impart the desired shape to the hair.
• At least one of these two compositions contains a compound of the formula (I).
• the reducing compositions generally contain the adjuvants which make it possible to present them in the form of lotions or in the form of a powder to be diluted in a liquid carrier.
• the reducing agent is most frequently a mercaptan, such as thioglycerol or thioglycolic acid or a derivative thereof.
• the concentration of the reducing agent is the concentration which is required to reduce a sufficient number of S--S bonds. These concentrations are well known and are described in standard works on cosmetology. For example, in the case of thioglycolic acid, the concentration is generally 1 to 11% by weight.
• the pH of these compositions for the first stage of perming generally varies from 7 to 10.
• the reducing compositions generally contain from 0.1 to 10% by weight, in particular 0.25 to 5%, of a compound of the formula (I).
• reducing lotions for the first stage of perming are most frequently aqueous solutions which can also contain pH modifiers, auxiliary reducing agents, such as sulphites, solvents, such as ethanol or isopropanol surface-active agents, perfumes and/or dyestuffs.
• auxiliary reducing agents such as sulphites
• solvents such as ethanol or isopropanol surface-active agents
• perfumes and/or dyestuffs are most frequently aqueous solutions which can also contain pH modifiers, auxiliary reducing agents, such as sulphites, solvents, such as ethanol or isopropanol surface-active agents, perfumes and/or dyestuffs.
• the oxidizing or neutralizing compositions applied in a second stage can contain the compound of the formula (I) and optionally conventional adjuvants.
• the compounds of the formula (I) can of course be used in all cosmetic formulations as an additive for imparting characteristics of easy combing-out, softness, glossiness and lightness to the hair, in addition to the properties which the compositions themselves are intended to impart.
• compositions according to the invention can also be applied to the skin and can adopt the various forms mentioned above; the quaternary ammonium derivatives give the skin a softness to the touch.
• compositions can contain the various cosmetic adjuvants which are normally used for the skin, in particular perfumes, dyestuffs, preservatives, sequestering agents, emulsifying agents, thickeners and sun filers.
• compositions constitute, in particular, treating creams or lotions for the hands or face, anti-sunburn creams, tinted creams, milks for removing make-up, shaving creams, foaming oils or liquids for the bath or shower, and deodorizing compositions, which can be prepared in accordance with conventional processes.
• the compounds according to the invention also possess other advantageous properties, such as bacteriostatic properties and surface-active properties.
• the mixture of amine and chlorine derivative is heated to 95° C.
• the reaction is highly exothermic and sudden thickening of the mixture takes place.
• Hot distilled water is added and the whole is kept at 90°-95° C. for one hour. The mixture becomes homogeneous and viscous.
• the acid number is 0.52, the amine number is 2.36 and the extent of reaction is 94%.
• the bis-quaternary compound prepared in this way corresponds to the formula ##STR5## in which R denotes a tallow alkyl chain.
• a tallow alkyl chain denotes a mixture of alkyl or alkenyl radicals having 10 to 20 carbon atoms, this mixture essentially comprising saturated groups having 16 carbon atoms and mono-, di- or tri-unsaturated groups having 18 carbon atoms.
• a further 2.65 g and 0.65 g of the bis-chloroacetylpiperazine derivative are added during the reaction.
• the mixture of amine and bis-chloroacetylpiperazine is heated to 90°-95° C. under nitrogen.
• the reaction is exothermic and the temperature rises to 100°-101° C., thickening of the mixture taking place.
• the acid number is 6.4 and the amine number is 1.1.
• the solution thus obtained is a viscous solution.
• the mixture of chlorine derivative and amine is heated to 90° C. in the course of one hour, under nitrogen, and is kept at 90°-95° C. for 1 hour 30 minutes.
• the reaction is exothermic and the mixture thickens.
• a 26.3% strength solution is in the form of a gel when cold.
• the mixture of amine and chlorine derivative is heated to 95° C.
• the mixture is diluted rapidly with hot water and the diluted mixture is kept at 95° C. for 2 hours.
• the mixture of amine and halogen derivative is heated to 90°-95° C.
• the acid number is 0.77, the amine number is 1.5 and the extent of reaction is 97%.
• Vaseline oil 25 g
• Partially oxyethyleneated cetyl/stearyl alcohol 30 g
• This composition which is used as a post-shampoo composition, is opaque, white in color and fluid, and has a viscosity of about 25 cps and a pH of 4.4. After the hair has been washed with a shampoo, rinsed and towel-dried, the hair milk described above is applied to the clean hair.
• This composition is appropriately spread over the whole head of hair and, after an interval of about 10 minutes, the hair is rinsed very carefully.
• wet the hair is easy to comb out and is soft to the touch.
• dry the hair is also easy to comb out and is soft, glossy, manageable, uncharged with static electricity and light.
• This composition which is used as a post-shampoo composition, is opaque, white in color and unctuous. It has a viscosity of about 400 cps. The pH of this product is 2.7. On applying this composition in accordance with the same procedure as that described in Example 1, it is also observed that, when wet, the hair is easy to comb out and is soft to the touch, and that, when dry, the hair is glossy, soft, easy to comb out and manageable.
• This composition is used as a post-shampoo hair milk. It is white in color and is fairly fluid, the viscosity being about 55 cps, and the pH is 6.1. In the same way as previously, it is found that the application of these compounds to the hair imparts a soft feel to the hair when wet, and, when dry, the hair is easy to comnb out, glossy, soft, manageable and uncharged with static electricity.
• Oxyethyleneated castor oil 200 g
• the pH is 4.9.
• This hair oil has the appearance and consistency of an oil, is limpid and of low viscosity and has a greasy feel.
• This oil is applied after shampooing, and, after an interval of a few minutes, followed by rinsing, the treated hair is easy to comb out, glossy, manageable and bulky.
• This composition can also be applied before shampooing, and left on the hair for an interval of 1 to 30 minutes.
• Oxyethyleneated castor oil 300 g
• Oxyethyleneated castor oil 220 g
• This oil is applied to wet hair before shampooing, and left on the hair for an interval of about 20 minutes.
• the hair is rinsed and then washed with a conventional shampoo and it is found that, when dry, the hair is easy to comb out, glossy and soft to the touch, has a good hold and is bulky.
• This balm has a very fluid, limpid appearance and a pH of 5.7.
• This composition is applied to clean wet hair which has been washed with a shampoo beforehand.
• This composition is in the form of a limpid fluid gel having a viscosity of about 200 cps.
• Gafquat 755 10 g
• This composition is in the form of a limpid treating lotion having a pH of 4.
• This composition is applied to dirty hair before shampooing. After rinsing and after shampooing, it is found, in the same way as previously, that the hair is easy to comb out, supple and manageable, without being weighed down.
• Partially oxyethyleneated cetyl/stearyl alcohol 30 g
• This composition which is used as a post-shampoo composition, has the appearnce of a white milk, a viscosity of about 380 cps after 24 hours and a pH of 5.
• Gafquat 755 5 g
• This composition which is used as a post-shampoo composition, is in the form of a limpid lotion having a pH of 6.35.
• the pH is adjusted to 6 with triethanolamine.
• This composition has a liquid, limpid and fluid appearance.
• the hair When wet, the hair is easy to comb out; when dry, the hair is glossy, soft to the touch, light and springy and is easy to comb out.
• R is a mixture of C 9 -C 12 alkyl radicals and n represents an average statistical value of about 3.5: 10 g
• the pH is adjusted to 5.
• the shampoo has the appearance of a thickened limpid liquid.
• the pH is adjusted to 5 with HCl.
• This composition has the appearance of a limpid gel.
• the mixture is applied to hair which has been washed and towel-dried, before setting it in waves.
• the hair is easy to comb out and soft to the touch. It is set in waves and dried.
• R denotes an oleyl group: 20 g
• R denotes an oleyl group: 20 g
• Pentasodium salt of diethylenetriaminopentaacetic acid (40% of active ingredient): 2.5 g
• This composition is applied to natural chestnut hair. After an interval of 10 minutes, the hair is rinsed; it is easy to comb out and has a soft feel. After wavesetting and drying, the hair has a particularly luminous mahogany sheen.
• This composition is applied to the hair.
• the hair is set in waves and dried; it is glossy and has volume and it is soft to the touch and easy to comb out.
• Citric acid 0.3 g
• This composition confers to the treated skin a softness to the touch.
• POLAWAX GP 200 oxyethyleneated stearyl alcohol sold by Croda.
• CELLOSIZE QP 4400 H hydroxyethylcellulose having a viscosity of 4,400 cps at 25° C. in a 2% strength solution (measured using a Brookfield No. 4 module), sold by Union Carbide.
• CROTEIN Q quaternized protein hydrolysate derivative sold by Croda.
• GAFQUAT 755 quaternary polyvinylpyrrolidone copolymer having a molecular weight of 1,000,000, marketed by GENERAL ANILINE.
• MERQUAT dimethyldialkyl chloride homopolymer sold by Merck.
• SINNOWAX 40 cetyl/stearyl alcohol containing 20% of alcohol oxyethyleneated with 15 mols of ethylene oxide, marketed by Henkel.
• UKANIL 25 linear fatty alcohol (C 13 -C 15 ) oxyethyleneated with 2.8 mols of ethylene oxide, sold by PUK.
• UKANIL 43 linear fatty alcohol (C 13 -C 15 ) oxyethyleneated with 7 mols of ethylene oxide, sold by PUK.
• SETACIN 103 SPEZIAL sodium hemi-sulphosuccinate of polyoxyethyleneated lauryl alcohol, containing 40% of active ingredient, sold by Zschimmer and Schwarz.
• METHOCEL F 4M hydroxypropylmethylcellulose sold by Dow Chemical.
• MIRANOL C 2M cycloimidazoline derivative of coconut oil (38% active material) of the formula ##STR34## sold by Miranol AMERCHOL L 101: Light mineral oil and a mixture of alcohol and sterols of lanoline sold by American Cholesterol Products Inc
• NATROSOL 250 HHR hydroxy ethyl ether of cellulose sold by HERCULES

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• 1979
  • 1979-09-17 LU LU81694A patent/LU81694A1/fr unknown
• 1980
  • 1980-09-16 CH CH6917/80A patent/CH647944A5/fr not_active IP Right Cessation
  • 1980-09-16 GB GB8029861A patent/GB2062460B/en not_active Expired
  • 1980-09-16 DK DK392280A patent/DK392280A/da not_active Application Discontinuation
  • 1980-09-16 NL NL8005170A patent/NL8005170A/nl unknown
  • 1980-09-16 BE BE0/202117A patent/BE885251A/fr not_active IP Right Cessation
  • 1980-09-16 DE DE19803034910 patent/DE3034910A1/de active Granted
  • 1980-09-16 AR AR282529A patent/AR226571A1/es active
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  • 1980-09-16 CA CA000360547A patent/CA1171859A/fr not_active Expired
  • 1980-09-16 US US06/187,954 patent/US4612188A/en not_active Expired - Lifetime
  • 1980-09-16 FR FR8019959A patent/FR2464710A1/fr active Granted
  • 1980-09-16 AT AT0463680A patent/AT381229B/de not_active IP Right Cessation
  • 1980-09-16 ES ES495091A patent/ES495091A0/es active Granted
  • 1980-09-16 IT IT68425/80A patent/IT1129254B/it active
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